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Branched-Chain Sugars. II. On the Configuration of Branched-Chain Sugars from Methyl 2-O-Benzoyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose
http://hdl.handle.net/10487/8163
http://hdl.handle.net/10487/8163d8e537ea-47b5-44b3-a44b-9e5600e8a2f9
| 名前 / ファイル | ライセンス | アクション |
|---|---|---|
佐藤・化学-002.pdf (4.2 MB)
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| Item type | 学術雑誌論文 / Journal Article(1) | |||||
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| 公開日 | 2011-01-28 | |||||
| タイトル | ||||||
| タイトル | Branched-Chain Sugars. II. On the Configuration of Branched-Chain Sugars from Methyl 2-O-Benzoyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 資源タイプ | ||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_6501 | |||||
| 資源タイプ | journal article | |||||
| 著者 |
吉村, 寿次
× 吉村, 寿次× Yoshimura, Juji× 佐藤, 憲一× Sato, Ken-ichi× Kobayashi, Kazuhiko× 辛, 重基× Shin, Chung-gi |
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| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | Stereoselectivities in diazomethane and nitromethane reaction of methyl 2-O-benzoyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose were examined. Reduction of the epoxidation product (2) gave an epimeric 3-C-methyl derivative in contrast with that obtained by the Grignard reaction. Comparison of NMR spectra of the corresponding di-O-acetate of the both epimers proved that 2 has the gluco-configuration. Ring-opening of the epoxide with alkali, methanolic ammonia, and acid gave the corresponding 3-C-hydroxymethyl, 3-C-aminomethyl (17), and de-O-benzylidenated product, respectively. Hydrogenation of the 3-C-nitromethyl derivative (21) obtained by nitromethane condensation, in the presence of Raney nickel, accompanied with benzoyl-migration to give 3-C-benzamidomethyl derivative (22). De-benzoylation of 22 with methanolic potassium hydroxide gave 3-C-aminomethyl derivative (26) and an orthoester-type compound. Comparison of 26 with 17 and their derivatives indicated that 21 has the allo-configuration. The both configurations were also supported by the optical rotation of 3-C-benzamidomethyl derivatives in cuprammonium solution. | |||||
| 書誌情報 |
Bulletin of the Chemical Society of Japan 巻 46, 号 5, p. 1515-1519, 発行日 1973-05 |
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| ISSN | ||||||
| 収録物識別子タイプ | ISSN | |||||
| 収録物識別子 | 0009-2673 | |||||
| 書誌レコードID | ||||||
| 収録物識別子タイプ | NCID | |||||
| 収録物識別子 | AA00580132 | |||||
| DOI | ||||||
| 関連タイプ | isIdenticalTo | |||||
| 識別子タイプ | DOI | |||||
| 関連識別子 | 10.1246/bcsj.46.1515 | |||||
| 著者版フラグ | ||||||
| 出版タイプ | VoR | |||||
| 出版タイプResource | http://purl.org/coar/version/c_970fb48d4fbd8a85 | |||||
| 出版者 | ||||||
| 出版者 | 日本化学会 | |||||
| 資源タイプ | ||||||
| 内容記述タイプ | Other | |||||
| 内容記述 | Article | |||||
